To Sir, with Love
by Southen-Fried-Penguin
Summary: Occasionally Dean finds himself in a place where all his emotions and insecurities come crashing down upon him all at once. Thankfully, he's found someone who knows just what he needs to get himself back on track.


_C'mon man, just breathe…._

Dean sat in his car, parked in front of a local fast food joint. He had just returned from a one-man job, routine salt and burn to keep an angry spirit from hurting anyone else in what it felt was its territory, and wanted to grab some cholesterol as a reward for himself. But the longer he sat there, the longer he felt panic begin to slowly rise inside him.

 _Not now, man. It wasn't that difficult….pull yourself together…._

He closed his eyes and tried to slow his breathing, but it wasn't helping. When he felt the first prickling of tears in the corners of his eyes, he knew he needed help. Dean grabbed his phone off the seat next to him and shot off a text to the only person who understood what he was going through and who more than once had managed to pull him out of it unscathed.

 **Wyd?**

The reply what almost immediate.

 **Call me.**

A few swipes of his fingers had his phone ringing in his ears, and after only 2 rings the only voice that could soothe him answered.

"What's wrong?"

"How'd you know?"

"Because your text wasn't your usual lame jokes. Where are you?"

"Chicken joint, just inside city limits."

"Are you ok?" Dean didn't reply. "Answer me!" the voice demanded.

"No." he whispered, trying to keep the waver out of his voice even though it was pointless. He couldn't hide anything from that voice who knew him so well. "I'm really losing it this time."

"Ok, just calm down." the soothing voice continued. "Are you still in the same motel? How far away are you?"

"Less than 5 miles. I can be back in my room in 10 minutes."

"I'm on my way." the voice replied, then the line went dead.

Dean threw his phone back on the passenger seat and carefully maneuvered his way around the parking lot until he could turn onto the main road, then started to drive as quickly as he could back to his motel. The hot tears were getting more insistent, and he had to wipe his eyes more than once to be able to see clearly enough to drive. It also didn't help that he managed to hit every red light on the way there, adding to his frustration and ramping up his anxiety. If he didn't get what he needed soon, he wasn't sure what he was going to do...and he didn't like the possibilities.

It would probably surprise a lot of people to learn that Dean Winchester, all around Badass, had a vulnerability that he carried with him, and that it managed to catch him unawares at the wrong times. On the outside he was always calm and collected, jumping into whatever frey was in front of him to protect the innocent, and never gave a second thought to himself or his own safety. He pushed himself well beyond his limits time and again, rarely slept and ate even less. It was the way he was raised, to be the perfect soldier without any weaknesses. He was told time and again that he was responsible for his little brother Sammy, that his safety would always be his number one concern, and the job was a close second. Himself? He never took the time to let out all his anger, frustrations and fears. Sam warned him for years that eventually it would come back to bite him in the ass but he had brushed it off, telling Sam that he was too young to try and replace Dr. Phil so he should shut it. Eventually Sam gave up, knowing that his brother would crack eventually and just hoped that he would be around to help when he finally did. Unfortunately it didn't happen that way, but when it finally happened there was _someone_ around who calmed him down and stopped him from breaking everything he could get his hands on. That night, they both discovered something surprising about themselves. They both were in need, and each had what the other desperately sought. And so began their little arrangement, kept secret from Sam of course. Some things just didn't need to be explained to others. They were both consenting adults so what happened between them stayed that way.

Dean finally pulled into the parking lot just as the rain began to pour from darkened skies. He huffed out a small laugh, finding it ironic that even the outside elements were matching his inner turmoil. He quickly grabbed his phone and keys before making the mad dash to his room, fumbling with the keys while trying to unlock the door. Once inside, the cold air from the constantly running a.c. hit his damp clothes, making him shiver. He made his way over to the unit and shut it off, while toeing off his boots and slipping out his wet flannel overshirt. After throwing the contents of his pockets on the small table he sat on the bed with his head in his hands and just waited. After a few moments he knew he was no longer alone. It wasn't footsteps outside his room or a knock at the door that alerted him to another presence, but the warm prickling on the the back of his neck told him that he was being watched. He quickly stood up and turned to face the figure standing in the shadows by the door, immediately feeling warm and safe.

"Hello Dean."

"Cas…." he whispered, his voice cracking as he called out to his savior. Sensing how far gone he already was, Castiel took two long strides across the room until he could gather Dean into his arms and just hold him tightly.

"Shhh….it's ok...shhh..." he said soothingly, allowing the broken hunter to cling to him as if clinging to life itself. His heart broke at feeling the sobs wracking the strong body in his arms but for now all could do was wait until Dean felt strong enough to talk to him. Castiel was content to wait as long as he needed to. He gently cradled Dean to him as he slowly backed them towards the bed and lowered them so that they could sit. He had the feeling that if it was possible Dean would crawl into his lap and curl himself into a ball for the rest of the night, and Castiel would let him if that was what he needed. For now, he just held Dean tightly, feeling the collar of his shirt become more and more wet with the sorrow pouring from his soul. He rocked him gently, and just waited.

Eventually, the sobs turned into sniffles then slowly disappeared altogether. Dean didn't make a move to sit up so he continued rocking him, slowly moving his hands in lazy circles along his back to soothe him. Cas continued to make small comforting noises in his ear, telling him it was going to be ok, telling him he was here for as long as he needed him, telling him that he would never leave.

Finally he felt Dean push himself away and Cas loosened his hold, allowing him to do so but not allowing him outside of arm's reach. He quietly watched as Dean wiped his face with both hands, trying to replace the stoic mask that he always wore for everyone. Cas grabbed his hands gently, not permitting him to retreat into himself until he was sure he had gotten everything out. "What happened Dean? Tell me." he inquired gently.

Dean heaved a deep sigh. "It was just everything all at once, you know." he whispered, trying to keep his voice steady. "The job, seeing innocent people hurt, the adrenaline pumping then crashing afterwards…..it just hit me." He bowed his head and almost looked embarrassed.

"If it was getting this bad, why didn't you tell me sooner?"

Dean shrugged his shoulders. "It didn't seem important at the time." he murmured. Castiel placed his fingers on Dean's chin and gently turned his face so that he could look him in those endless green eyes while rubbing the pad of his thumb across the bottom lip he knew was so soft and inviting.

"Dean, your well being is very important to me. I'm disappointed in you for letting it get this far." He could see Dean's face fall at being told he had made a mistake. Cas knew Dean didn't admit mistakes easily, but also knew that Dean found enough comfort in their arrangement to be more open than he would be with anyone else. He used that to give the eldest Winchester the solace and reassurance he wouldn't accept from anyone else. Not even his own brother. "Are you feeling better, or do you need…..more?" he asked, allowing Dean to dictate Cas's next actions.

He watched as Dean's eyes began to water slightly, threatening to spill over once again. "Help me Cas," he pleaded. "Help me stop thinking...about everything."

Castiel leaned forward and just barely brushed his lips against Dean's. "I've got you, you're safe." he promised. He could see the trust glowing in those eyes that watched him so intently. It humbled him, knowing that this amazing man put his most sacred possession in Castiel's hands. It was a responsibility he would never take lightly, and he certainly had no intention of doing so now.

He stood up and walked a few paces away into the open part of the room before turning back to the broken figure still perched on the bed. He squared his shoulders and dropped his voice a full octave. "Kneel." he commanded.

Dean's response was immediate. He instantly dropped to his knees and sat lightly back on his heels, keeping his hands resting lightly on his thighs, palms facing upwards while he trained his gaze at the floor in front of him. Castiel couldn't help the small smirk that turned up one corner of his mouth. Dean had always been so beautiful to him, but since their arrangement began he had been given permission to put Dean in any position or situation he had seen fit. The results were always….breathtaking.

He removed his trench coat and suit jacket, slinging them haphazardly towards a nearby chair, not really caring where it landed. He began to roll up his sleeves to just above his elbow as he began to step closer. With each step, he heard Dean's breathing slowly escalating. It still thrilled him to know that Dean enjoyed this as much as he did. "Do you know why you are here Dean?" he asked keeping his voice low but forceful. As expected, Dean remained silent until he was given permission. "You may speak."

"I'm here because I need your help, Sir. You are the only one I trust to help me."

Cas felt his insides grow warm with affection at his words. "And why do you need my help?" he continued.

"Because I allowed myself to become overwhelmed, Sir."

"And what are you supposed to do before that happens Dean?"

"I'm supposed to talk to you."

"And you didn't."

"No Sir."

"Meaning…?" Cas prompted. He watched those broad shoulders slowly slump at the implication.

"I disobeyed an order."

"And disobedience deserves what?"

"Punishment, Sir."

By now he was standing within a foot of Dean's kneeling figure, and he just stood there, allowing his presence to both intimidate and comfort. He knew that anticipation only heightened everything for the both of them, and no matter how badly he wanted to just _take_ , he always reigned in his eagerness to allow Dean to get what he needed as well.

"Look at me."

Dean slowly allowed his gaze to travel upwards, following the muscled thighs he knew were hidden underneath the ill fitting slacks, to the torso he had become well acquainted with over the past months, finally settling on the face that gazed at him with stern affection. He felt a small shiver travel his spine at the eyes that bore into him with the intensity of a thousand suns, lighting up his insides with a warm and fuzzy feeling. Despite that shiver, Dean knew that there was nowhere safer in the entire universe than being in the gaze and the hands of his Angel.

He watched as Castiel slowly began to loosen his tie, his movements precise and methodical. Once the knot was gone he let it hang loosely around his neck instead of removing it. They continued to stare at each other, the moment continuing to stretch on along with the deafening silence. Dean started feeling self-conscience about looking in the eyes of the one who had control over him but he didn't dare disobey again.

"Why?" Castiel suddenly asked. Dean just blinked in confusion.

"Sir?"

"Why did you disobey me?"

"I don't know, Sir."

"That answer is not acceptable. Try again."

Dean swallowed. "I thought I could handle it."

"And you were wrong. By ignoring your orders, you put yourself in danger. Mentally and physically. That is something I cannot allow to go unpunished." Castiel took a step back. "On your feet." He watched with impassive eyes as Dean pushed himself off the floor and awaited further instructions. He only paused for a moment before commanding him again. "Strip."

Dean immediately grabbed the hem of his t-shirt and pulled it up and over his head, baring his expanse of golden skin to Castiel's gaze. He let it drop to the floor before reaching for the fly of his jeans, popping the button and pulling the zipper open. He pulled both his jeans and boxers down in one swift movement, pooling them at his feet before stepping out of them and kicking them to the side. Everything he had was now laid bare, both his body and his emotions. His cock was hard and standing at attention tightly against his belly, the small drop of precum glistening in the dim lighting of the room.

Castiel's heart hammered in his chest at the sight. He never got tired of seeing Dean putting himself on display for him. He inhaled sharply to calm himself so that he could continue as unaffected as possible. "You may no longer look at me. Avert your eyes until I tell you otherwise." Dean's gaze immediately dropped to the floor once again. Cas couldn't help but feel pride at his obedience. "Turn around, hands behind your back." Dean quickly complied.

He quickly walked into Dean's space, crowding so close to him that he could feel the heat radiating from the sun-kissed skin. Cas then slowly removed the tie still hanging limply around him, and after taking Dean's hands in one hand, he began to tie them together with the other. The knot was simple enough to be removed easily if needed, but also strong enough to hold him still for what was about to come. Before he moved to the next phase, he couldn't help pressing soft kisses across Dean's shoulders. He knew Dean often felt the weight of the world on them. However, in this moment, he wanted them to feel nothing except the weight of his affections. "You are so beautiful." he couldn't help but murmur in Dean's ear, delighting in the goosebumps that quickly appeared on his skin.

Those words caused a calm to come over Dean that he only felt when he was in Cas's control. In these moments, nothing else mattered. The rest of the world could explode around him and he would never even notice. All his insecurities and his fears vanished completely, and he was no longer a broken man who second guessed if his decisions were the right ones. Here, he was safe, cherished, even worshipped. His mind was blessedly blank except for the sensations that Castiel created inside of him, and it was exactly what he needed. "Thank you Sir." he said quietly.

He yelped when Cas brought his hand in a quick slap across his ass, the sound resonating in the quiet room as warmth blushed on his skin. "No more talking without permission." Cas growled in his ear. Dean nodded his acknowledgement of the command but wisely kept silent.

Castiel moved to stand in front of him but Dean still kept his eyes lowered, staring at his bare toes on the threadbare carpet. He could hear the springs of the mattress quietly squeak as Cas took a seat on the very corner he was sitting on minutes ago. The next thing he knew, Cas was pulling him across his lap. He appreciated the fact that since his hands were still tied Cas helped him get situated without allowing him to fall on the floor. Cas widened his legs a little more, so that one thigh was pressed firmly against Dean's chest while the other was nestled against his groin, completely trapping his cock against his stomach. The slightest movement would cause a delicious friction from Castiel's slacks against the sensitive skin of his dick, but he dared not move. His concentration on keeping completely still had him panting.

Castiel began gently rubbing the tender and smooth skin of Dean's ass, beautifully on display for him to do as he pleases. He was hyper aware of the change in Dean's breathing and couldn't help the smirk that crossed his face. Dean knew what was coming, but he decided to have a little extra fun with it.

"You will be punished for your disobedience, make no mistake. But I'm not without leniency. I'm going to give you a choice. You may choose between 20 strikes of my usual force, or you may drop that number to 10, but by doing so you will be allowing me to push your pain tolerance as far as I can." Dean's gulp was audible. "Choose quickly before I choose for you. I'm impatient when it comes to any opportunity to paint your ass red."

Dean's answer was almost instant. "I choose 10, Sir."

Castiel was both surprised, and yet not surprised at all. He knew that Dean enjoyed having his limits pushed, but he also knew Dean was full of safe hatred sometimes. If he was choosing the harsher punishment as a way to punish himself, Castiel simply wasn't going to allow it. Dean's punishments belonged to him, and only him. He had to know for sure.

He tilted Dean's face so that he could look at him. "Why 10 Dean?" he asked. "You may speak."

Dean looked at him with sorrowful eyes. "Because I trust you, Sir. You would never hurt me beyond my limitations."

Castiel couldn't help the way his heart melted with those words. He gently carded his left hand through Dean's honey brown hair. "You're so good for me." he praised as he leaned down to press a kiss on Dean's left shoulder blade. He gave Dean a reassuring smile as he straightened back up and proceeded to get back to business. Castiel used his left hand to grip his tie still holding Dean tightly while he right hand continued with its soothing motions. "What is your safeword?" he demanded. "Speak!"

"Kansas."

"Very good. You will count out loud for me. If you fail to count each hit, I will start over. Nod if you understand."

Dean nodded. He was ready.

"Let's begin." Within seconds Cas delivered an open palmed smack on the meatiest part of Dean's right cheek. It wasn't particularly hard, yet, but it left a pinkish mark behind that thrilled Cas.

"One."

"Good boy." Castiel praised. The next blow was decidedly harder and delivered on the left side. He felt Dean jump slightly at the impact, causing his blood to warm at the sight.

"Two."

The next ten minutes were filled with the sounds of skin hitting skin and Dean moaning out numbers as best he could. Every hit that kept coming was harder than the last, causing Dean to writhe in Cas's lap, both from the pleasure and the pain. He felt the heat on both his ass and his upper thighs from Cas methodically spreading each strike so as not to overlap another. The friction caused by Cas's thigh in his groin was almost becoming unbearable. Every inch of him was becoming over sensitive from the endorphins flooding his system, and he wanted nothing more than to float away into the oblivion that was clouding his mind. But Cas wasn't finished yet. He still had one more strike to go. He could do this, he could be good. For Cas.

Castiel watched as Dean's skin transformed before his eyes, watching areas change from a blushing pink to an angry red. His handprint marked that beautiful landscape, claiming the man underneath him as his. He knew Dean's reaction to each of the strikes from his hand, could feel his cock leaking and soaking his slacks with copious amounts of precum. Any other man would have cracked by now and either safeworded or would have come already, but not Dean. He was perfect. And he deserved a reward.

"Last one Dean. You're doing so beautifully. Always perfect for me. Because you did so well, I'm rewarding you. As soon as you feel me strike you for the last time, you will let go and you will come for me. I want to hear it ripped out of you." What he _didn't_ tell Dean was that he was going to cheat a little. Not only was the last strike _not_ going to be the hardest one, but if a tiny bit of his grace just happened to leave his hand and electrify his prostate, well...Dean would never know.

He brought his hand down firmly with the final strike, aimed directly in the center. Instead of removing it quickly as he had before he let it rest there, feeling the heat from the abused flesh soak into his skin. His hand tingled slightly as a tiny tendril of his grace entered Dean's body and hit its target head on.

Dean threw his head back and _howled_ Castiel's name _,_ his orgasm ripping him to pieces and leaving him a quivering mess of nerve endings and liquefied muscles. Thick white ropes covered his chest and Cas's legs. Minutes passed before Dean showed any signs of slowly coming down off his high. Before he crashed completely, Cas helped him stand on wobbly legs and quickly released his bound hands. The blue tie fell unnoticed to the floor as Castiel swept Dean into his arms and settled in against the headboard, allowing Dean to curl into him completely. He tucked Dean's head under his chin and held him tightly while ignoring the mess covering them both. Cas slid his hands over Dean, soothing him with praise the entire time.

"I'm so proud of you Dean. You are breathtaking and so perfect. You're so good for me." he whispered over and over until he felt Dean completely relax and soft snores could be heard coming from the man in his arms. With a quick wave of his hand he cleaned them both up then carefully situated them underneath the blankets, becoming the big spoon as he settled an arm around Dean and pulled him as close as possible. He may not have the need for sleep but he floated on a wave of peace and contentment. Castiel closed his eyes and just drifted.

The next thing he knew bright light was streaming through the small crack in the curtains. Morning had come without him realizing it. Perhaps he had dozed off after all. He couldn't help but smile as the memories from yesterday washed over him and he reached for the man next to him.

The bed was cold and empty.

Alarm shot through him as he sat up and looked where Dean should have been. Instead of the hunter he found a single red rose and a note.

 _To Sir, with Love_

 _Thank You for everything_

 _P.S. Duty calls. See you at the bunker._

 _Dean_

Castiel couldn't help the smile on his face as he picked up the delicate blossom and inhaled the sweet scent. He got up and retrieved his tie, jacket and trench coat, returning them to their proper places. He carefully folded the note and placed it in the inner pocket of his jacket, near his heart.

 _Love._

The smile never left his face as he flapped his powerful wings, and was gone.


End file.
